Wang C, * Ozaki T, Takita R, Uchiyama M. * RIKEN, Advanced Science Institute, Saitama and The University of Tokyo, Japan
Aryl Ether as a Negishi Coupling Partner: An Approach for Constructing C–C Bonds under Mild Conditions.
Chem. Eur. J. 2012;
18: 3482-3485
Key words
zinc - nickel - aryl ethers - C–O activation - cross-coupling
Significance
The first nickel-catalyzed cross-coupling of aryl ethers with aromatic zincates via C–O bond cleavage is described. The corresponding biaryls are obtained in moderate to good yields. Electron-rich coupling partners furnish higher product yields than reagents containing electron-withdrawing groups.
Comment
It is noteworthy that, besides the methoxy moiety, this methodology may be extended to ethyl and isopropyl ethers as well. Furthermore, this protocol allows a facile conversion of chiral substrates into the corresponding biaryls without racemization.
